Perfecting the Preppy Style Over 50

The preppy look originated in the early 1900s with collegiate and prep-school menswear (thus, the moniker). Signature items included blazers, polos, chinos, oxford shirts, tennis sweaters, loafers.

Over the decades, fashion designers ranging from Ralph Lauren to Tommy Hilfiger and Tory Burch have celebrated preppy style. The Preppy Handbook, published by Lisa Birnbach in 1980, was intended as a kind of send-up — but it also served as a how-to manual for many people unfamiliar with the look.

Today’s sporty, slightly rumpled preppy aesthetic is a bit more androgynous, sexy and playful. Think more Diane Keaton in Annie Hall vs. anyone named Muffy. (In other words, skip the grosgrain headbands, cashmere twinsets and pearls. We’re not taking about the pink-and-green Lilly Pulitzer kind of preppy here.)

This is about clothing inspired by the yacht club, tennis club, country club or college campus — but, today, these items push the old house rules. Their fit might be slightly off ... the blazer may be a little shrunken or oversized; the chinos, slouchy or cropped.

It’s a terrific look for autumn weekends, whether you spend them browsing at an urban flea market, meeting girlfriends for lunch or watching your grandkids’ soccer games.

How to pull it off

Add one decidedly non-preppy element to your look: Say, wear a sexy silk shirt half-tucked into baggy khakis. Or pair your fisherman sweater and cropped jeans with a kitten heel.

You can, of course, embrace the whole boyish aspect: blazer, striped shirt, chinos, crewneck, driving shoes. But remember to wear lipstick — and maybe a chain necklace, or some stacked bracelets, or small drop earrings. One feminine detail goes a long way.

The Elements of Preppy Style: Worthy of investment because they stand the test of time

The navy blazer​

A well-tailored jacket upgrades your basic jeans and chinos — and also pairs beautifully with trousers or a pencil skirt for more formal occasions.​

The cable-knit sweater​

A textured knit adds visual interest to your look when worn with casual pants. Push up the sleeves for extra panache.​

The slouchy chino​

Cut more like a trouser than your standard-issue khakis, these can work with sneakers, loafers, even slingback pumps.​

The striped cotton shirt​

A crisp button-down in a menswear stripe spells polish. Pop the collar to up the preppy factor.​

The suede driving moccasin​

Lightweight and flexible, the driving shoe was an instant status symbol for men when it was introduced in Italy in 1963. Today, it still hints of prestige — and can add some fun color to your weekend neutrals.​

Final word

Make no apologies for dressing like a prepster even if you aren’t. Like F. Scott Fitzgerald’s character Jay Gatsby or fashion designer Ralph Lauren (formerly Ralph Lifshitz, born and raised in the Bronx), we’re Americans — we reinvent ourselves!